Plant growth regulators

ABSTRACT

New agents for influencing plant growth and based on a composition of (a) a substituted heterocyclic ammonium salt and (b) a substituted carboxylate of 3-phenoxybenzyl, and processes for influencing plant growth with these agents.

The present invention relates to new and valuable agents for influencingplant growth, based on compositions containing morpholinium orpiperidinium salts and substituted carboxylates of 3-phenoxybenzyl, andprocesses for influencing plant growth with these agents.

It is known to use N,N-dimethylmorpholinium chloride (German PrintedApplication DAS No. 1,642,215), N,N-dimethylpiperidinium chloride(German Laid-Open Application DOS No. 2,207,575),N,N-dimethylpyrrolidinium chloride and N,N-dimethylhexahydropyridaziniumbromide as growth regulators. Reduction in growth height is one of theeffects achieved with these active ingredients.

I have now found that agents for influencing plant growth based on asubstituted heterocyclic N,N-dimethylammonium salt selected from thegroup consisting of the N,N-dimethylmorpholinium salt, theN,N-dimethylpiperidinium salt, the N,N-dimethylpyrrolidinium salt andthe N,N-dimethylhexahydropyridazinium salt have an improved biologicalaction if they additionally contain a compound selected from the groupof substituted carboxylates of 3-phenoxybenzyl of the formulae ##STR1##

The agents may contain two or more of the abovementioned activeingredients. The carboxylates may also be in the form of their variousisomers, e.g., cis-trans isomers or optical isomers, or mixturesthereof.

Preferred salts of the substituted heterocyclic N,N-dimethylammoniumcompounds are the halides, for example the bromides and, preferably, thechlorides.

The ratio of one or more salts from the group of the substitutedheterocyclic N,N-dimethylammonium salts to one or more activeingredients from the group of the carboxylates may vary within widelimits, for instance from 1:10 to 20:1 or from 1:8 to 12.9:1 parts byweight. Compositions having a weight ratio of from 1:2 to 1.6:1 alsohave a good effect. The agents according to the invention act on plantssuch as cereals and cotton. The action achieved by the compositionsaccording to the invention is superior to that obtained by addingtogether the individual actions of their components, i.e., it issynergistic. This synergistic action is particularly evident in the caseof cotton, where a considerable reduction in height is achieved.Additional effects are also observed, for instance the desiredabscission of foliage shortly before the bolls are ripe, and an increasein yield, for example as a result of the greater weight of theindividual bolls. The compounds from the group of the carboxylates alsohave an insecticidal action. Application rates for the agents accordingto the invention range for instance from 50 to 500 g of activeingredient composition per hectare. The compositions according to theinvention may for example in the case of cotton be applied shortlybefore or shortly after the onset of flowering. In certain areas, asecond treatment is, depending on the weather conditions, advantageousduring full blossom and up to the end of the bloom period. The agentsmay also be used as seed dressings or for treating the soil before orafter emergence of the plants.

Application may be effected for instance in the form of directlysprayable solutions, powders, suspensions, dispersions, emulsions, oildispersions, pastes, dusts, broadcasing agents, or granules by spraying,atomizing, dusting, broadcasting or watering. The forms of applicationdepend entirely on the purpose for which the agents are being used; inany case they should ensure a fine distribution of the activeingredient.

For the preparation of solutions, emulsions, pastes and oil dispersionsto be sprayed direct, mineral oil fractions of medium to high boilingpoint, such as kerosene or diesel oil, further coal-tar oils, etc. andoils of vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons such as benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives suchas methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,etc., and strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes,oil dispersions or wettable powders by adding water. To prepareemulsions, pastes and oil dispersions the ingredients as such ordissolved in an oil or solvent may be homogenized in water by means ofwetting or dispersing agents, adherents or emulsifiers. Concentrateswhich are suitable for dilution with water may be prepared from activeingredient, wetting agent, adherent, emulsifying or dispersing agent andpossibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of ligninsulfonic acid, naphthalenesulfonic acids,phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkylsulfonates, alkali metal and alkaline earth metal salts ofdibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcoholsulfates, alkali metal and alkaline earth metal salts of fatty acids,salts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof sulfated fatty alcohol glycol ether, condensation products ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensation products of naphthalene or naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenol polyglycol ethers,alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol esters, lignin, sulfite waste liquors and methylcellulose.

Powders, dusts and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silicic acid, silica gels,silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground plastics, fertilizers such as ammonium sulfate,ammonium phosphate, ammonium nitrate, and ureas, and vegetable productssuch as grain flours, bark meal, wood meal, and nutshell meal,cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % byweight of active ingredient.

There may be added to the compositions oils of various types,herbicides, fungicides, nematocides, insecticides, bactericides, traceelements, fertilizers, antifoams (e.g. silicones), growth regulators,defoliants, agents for promoting simultaneous ripening, synergists,surfactants and antidotes.

The surprising action of the agents according to the invention will beapparent from the following examples. In the experiments, cotton(Gossypium hirsutum) of the DPL 216 variety was sown and treatedapproximately two months after sowing with the agents according to theinvention in aqueous solution (the amount of water applied being about600 liters per hectare). Approximately two months after the treatment,the growth height of the plants and, in one instance, the weight of thebolls at harvesttime were ascertained. For comparison, untreated plantsand plants only treated with one active ingredient were used.

    __________________________________________________________________________           Application                    Average boll                            Active rate           Growth height   weight                                  ingredient                                                                           g/ha   Weight ratio                                                                          cm   %    +/- cm                                                                              gr. %                                   __________________________________________________________________________    Example 1                                                                     Untreated                                                                            0      --      183.8                                                                              100  0                                             C(x)   1940   --      131.0                                                                              71   -52.8                                         B(x)   150    --      189.5                                                                              103  + 5.7                                         C      1940                                                                   + B    150     12.9:1 125.8                                                                              68   -58.0                                         Example 2                                                                     Untreated                                                                            0      --      183.8                                                                              100  0                                             C      230    --      169.2                                                                              92   -14.6                                         B      150    --      189.5                                                                              103  + 5.7                                         C      230                                                                    + B    150    1.5:1   158.8                                                                              86   -25.0                                         Example 3                                                                     Untreated                                                                            0      --      89.8 100  0     6.2 100                                 C      230    --      82.0 91   - 7.8 6.2 100                                 B      150    --      93.0 104  + 3.2 5.6  90                                 C      230                                                                    + B    150    1.5:1   78.8 88   -11.0 6.6 106                                 __________________________________________________________________________     (x)C = N',N-dimethylmorpholinim chloride                                      (x)B =                                                                        3-phenoxybenzyl-(+)-cis-trans-2,2-dimethyl-3-(2,2-dichloro-vinyl)-cyclopr    pane carboxylate                                                          

           Application                                                            Active rate           Growth height                                           ingredient                                                                           g/ha   Weight ratio                                                                          cm   %    +/- cm                                        __________________________________________________________________________    Example 4                                                                     Untreated                                                                            0      --      183.8                                                                              100  0                                             C      138    --      168.0                                                                              91   -15.8                                         B      150    --      189.5                                                                              103  + 5.7                                         C      138                                                                    + B    150    1:1     157.5                                                                              86   -26.3                                         Example 5                                                                     Untreated                                                                            0      --      86.5 100  0                                             A(x)    75    --      79.8 92   -6.7                                          B(x)   150    --      88.8 103  +2.3                                          A       75                                                                    + B    150    1:2     74.5 86   -12.0                                         Example 6                                                                     Untreated                                                                            0      --      183.8                                                                              100  0                                             A       25    --      166.5                                                                              90   -17.3                                         B      200    --      191.2                                                                              104  + 7.4                                         A       25                                                                    + B    200    1:8     162.8                                                                              88   -21.0                                         __________________________________________________________________________     (x)A = N',N-dimethylpiperidinium chloride                                     (x)B =                                                                        3-phenoxybenzyl-(+)-cis-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopro    ane carboxylate                                                           

I claim:
 1. A plant growth regulator comprising a composition of (a) asubstituted heterocyclic N,N-dimethylammonium halide salt selected fromthe group consisting of the N,N-dimethylmorpholinium salt and theN-N-dimethylpiperidinium salt, and (b) a compound selected from thegroup of substituted carboxylates of 3-phenoxybenzyl of the formulae##STR2## wherein the ratio of (a) to (b) is from 1:10 to 20:1.
 2. Anagent for influencing plant growth, comprising a composition of (a)N,N-dimethylpiperidinium chloride and (b)3-phenoxybenzyl-(+)-cis-trans-2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropanecarboxylate, wherein the ratio of (a) to (b) is from 1:10 to 20:1.